Neosaxitoxin

Neosaxitoxin (NSTX) is included, as other saxitoxin-analogs, in a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs). The parent compound of PSTs, saxitoxin (STX), is a tricyclic perhydropurine alkaloid, which can be substituted at various positions, leading to more than 30 naturally occurring STX analogues. All of them are related imidazoline guanidinium derivatives.

Neosaxitoxin
Names
IUPAC name
[(3aS,4R,10aS)-5,10,10-Trihydroxy-2,6-diiminooctahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
Other names
1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-4-(((aminocarbonyl)oxy)methyl)-3a,4,5,6,8,9-hexahydro-5-hydroxy-6-imino-, (3aS,4R,10aS)-; 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-4-((aminocarbonyl)oxy)methyl-3a,4,5,6,8,9-hexahydro-5-hydroxy-6-imino-,(3aS,4R,10aS)-; 1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-4-((aminocarbonyl)oxy)methyl-3a,4,5,6,8,9-hexahydro-5-hydroxy-6-imino-,(3aS-(3aalpha,4alpha,10aR*))-
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.237.662
KEGG
UNII
  • InChI=1S/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,12,19-21H,1-3H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1
    Key: PPEKGEBBBBNZKS-HGRQIUPRSA-N
  • InChI=1/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,12,19-21H,1-3H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1
    Key: PPEKGEBBBBNZKS-HGRQIUPRBS
  • C1CN2C(=N)N([C@H]([C@H]3[C@]2(C1(O)O)NC(=N)N3)COC(=O)N)O
Properties
C10H17N7O5
Molar mass 315.286
Hazards
GHS labelling:
Danger
H300
P264, P270, P301+P310, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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